A short summary of the unbelievable Silk Road story as captured in Nick Bilton’s American Kingpin

Can I make a confession?

Seriously, can I come clean about something?

For all of the reading I do, I don’t think that I’ve ever, honest-to-God, read an entire book from the very first page all the way through the very last.

Straight up.

I read non-fiction, so by page 200 I usually get the idea and can move on with my life. I skip around, quit boring books, and just never quite finish stuff. Sue me.

But that all changed this weekend…

I picked up Nick Bilton’s American Kingpin and quite literally could not put it down.

Look at my Kindle stats:

The data don’t lie.

American Kingpin is the true story behind The Silk Road — you remember: the website on the “Dark Web” where you used to be able to buy any drug imaginable?

Oh, and not just drugs. You could buy weapons, hitmen, cyanide, human organs…

The Silk Road started as a libertarian “side hustle”

As you can imagine, the backstory of how the site came to be is nutty:

An idealistic 20-something, Ross Ulbricht, builds a website — a completely unregulated black market “Amazon.com” — to express his libertarian values and sets out to unseat what he believes is a cruel, unjust government (the U.S. government).

Ulbricht starts to build his Dark Web drug marketplace while running his friend’s bookstore. The site was a side hustle of sorts.

But before long, it takes off and starts to occupy more and more of his time.

Soon, he’s processing millions of dollars each month through his site (people love drugs!) and has built something that history’s most esteemed drug lords and startup founders alike would envy.

From hacker to kingpin

Ulbricht quickly transforms from an idealist into a cold, pragmatic, Walter White-type character who relishes the challenge of building his billion-dollar drug empire.

Ulbricht ditches his day job to go full-time on The Silk Road and begins sliding deeper and deeper into “evil” territory as his power and wealth skyrocket.

For example, here’s an ethical fork in the road he faced:

“Question for you,” one of his employees had asked at the time. “Do we allow selling kidneys and livers?”

Would you like to guess his answer?

Mhmmm…

None of Ulbricht’s friends realize what he’s up to…

In true Breaking Bad fashion, the Silk Road founder carries on a normal-ish existence to the outside world for most of the story.

He lives in San Francisco with some roommates, goes camping on the weekends, works from coffee shops, and generally lives a life indistinguishable from a solo startup founder in SF (which I guess he technically was…).

Indeed, Ross Ulbricht, the leader of one of the largest drug empires in history, was indistinguishable from an SF “tech bro”:

After breakfast each morning, while René and Selena sauntered off to work, their new roommate, Ross, would wave good-bye and wander town the street to a nearby coffee shop to oversee his drug empire.

The government begins hunting for him

Before long, every three-letter agency in the government starts to hunt the person or people running The Silk Road.

They hit nothing but dead ends for roughly two years, until a semi-rogue DEA agent befriends “Dread Pirate Roberts” (Ulbricht’s online persona), chatting and emailing him frequently, weaving a fabricated backstory about being an experienced large-scale drug smuggler.

Ulbricht hires the cop to carry out a hit on a former Silk Road employee, which he “does,” successfully convincing Ulbricht that he’s loyal and reliable.

But then the cop crosses an unimaginable ethical line and… well… you know what, sorry. You’re just going to have to read this thing if you want to know.

This story, which, again, is true, rivals some of the best crime novels. There are dirty cops. Hitmen. Drug dealers. And almost as many ethical gray areas as there are characters.

But as compelling as the story is, the storytelling is worth its own mention. The book is written as narrative non-fiction and the details that that the author chose to include are brilliant.

Anyway, if you’re into these sorts of nonfiction narrative stories, here’s the link: American Kingpin.

If you’re not in the market for a page-turner, at least add the Silk Road founder on Linkedin.

… but don’t be surprised if it takes a little while to get a response. He’s in prison for the rest of his life.

P.S. This is an excerpt from an email that was sent to the Stew’s Letter list.

Hedonism didn't kill God, rationality did; and there are few more rational thinkers in this galaxy than the author Sam Harris.

For 20 years, Sam Harris has been launching truth-seeking missiles into the heart of humanity's most cherished traditions.

I first heard Sam Harris on a Tim Ferriss podcast in 2014 and remember thinking, "this is the most rational and articulate person I have ever listened to."

Since then, I've read every one of his books, watched just about every YouTube video he's in, and even hung out with him a couple of times at TED.

But after years of following Harris, I still think some of his best insights are in his first book The End of Faith -- an unrelentingly rational book that fundamentally shaped how I think about religion.

Here are six mind-stretching Sam Harris quotes from The End of Faiththat deleted the space previously reserved in my mind for "God":

“The danger of religious faith is that it allows otherwise normal human beings to reap the fruits of madness and consider them holy.

Because each new generation of children is taught that religious propositions need not be justified in the way that all others must, civilization is still being besieged by the armies of the preposterous.

We are, even now, killing ourselves over ancient literature.

Who would have thought something so tragically absurd could be possible?”

“Tell a devout Christian that his wife is cheating on him, or that frozen yogurt can make a man invisible, and he is likely to require as much evidence as anyone else, and to be persuaded only to the extent that you give it.

Tell him that the book he keeps by his bed was written by an invisible deity who will punish him with fire for eternity if he fails to accept its every incredible claim about the universe, and he seems to require no evidence what so ever.”

“Anyone being flown to a distant city for heart-bypass surgery has conceded, tacitly at least, that we have learned a few things about physics, geography, engineering, and medicine since the time of Moses.”

“The doors leading out of scriptural literalism do not open from the inside.

The moderation we see among nonfundamentalists is not some sign that faith itself has evolved; it is, rather, the product of the many hammer blows of modernity that have exposed certain tenets of faith to doubt.”

“It is time we admitted, from kings and presidents on down, that there is no evidence that any of our books was authored by the Creator of the universe.

The Bible, it seems certain, was the work of sand-strewn men and women who thought the earth was flat and for whom a wheelbarrow would have been a breathtaking example of emerging technology.

To rely on such a document as the basis for our worldview, however heroic the efforts of redactors, is to repudiate two thousand years of civilizing insights that the human mind has only just begun to inscribe upon itself through secular politics and scientific culture.

We will see that the greatest problem confronting civilization is not merely religious extremism: rather, it is the larger set of cultural and intellectual accommodations we have made to faith itself.”

“We live in a world of unimaginable surprises - from the fusion energy that lights the sun to the genetic and evolutionary consequences of this light’s dancing for eons upon the earth - and yet paradise conforms to our most superficial concerns with all the fidelity of a Caribbean cruise.

This is wondrously strange.

If one didn't know better, one would think that man, in his fear of losing all that he loves, had created heaven, along with its gatekeeper God, in his own image.”

Now, you probably guessed it by now, but, yep… that entire two minute video was narrated using artificial intelligence.

As in…a human did not speak a word in that video. A machine learning program generated the entire narration.

You just heard a demo of one of the most advanced text-to-speech programs in existence today…built by two guys you've never heard of in Seattle.

Their program “reads” sentences off of a script and produces the sounds that it believes a human would make if they were reading the same sentences aloud.

(Okay that’s a little vague, but you get the general idea…)

The result is what you just heard: a humanlike voiceover track generated entirely using artificial intelligence.

Pretty cool, right?

Their technology rivals the bleeding-edge research being done at companies like Google.

Seriously, here's a side-by-side demo of Google’s best-of-market WaveNet voice reading the same paragraph as two of WellSaid's voices: WellSaid vs. Google.

Google is working on better voices (look up “Tacotron 2”), but they're not commercially available yet -- also, when you read the “fine print” in the research papers themselves you’ll realize that their technology has far more limitations than meets the…ear.

“So, all of that’s cool, but what would people even use this technology for?”

Have you ever done something so moronic that you’ve found it difficult to believe that any human, much less the human whose conscious experience you happen to occupy, could be so stupid?

For example, I attempted — and failed — to cook four Trader Joe’s chicken nuggets yesterday afternoon. The instructions fit into one sentence:

Preheat oven to 425 degrees and place nuggets on center rack for 20 minutes (this is impossible to screw up, you dunce).

Incredibly, I managed to screw it up. I neglected to set a timer, started to work on other things, and about 45 minutes later was notified that lunch was ready as a cloud of smoke and the smell of scorched chicken nugget filled the apartment. Classic.

This sort of thing happens all the time. I am terrible with navigating the minutia of daily life and always have been. I lose keys, burn chicken nuggets, pour myself drinks and forget about them, and email myself reminders only to be surprised that I have a new email after I hit "send." I live inside my own head, caught in whatever idea happens to hold the reigns at that moment, which often diverts my attention from whatever is unfolding right in front of me.

My natural impulse over the years has been to work hard at “fixing” this glaring inadequacy in my character and to become more functional in the elements of life that I consider boring but necessary. But after years of consciously trying to improve this side of myself, I have made essentially zero progress.

"I wished to live without committing any fault at any time"

I felt pretty frustrated until recently reading the autobiography of Benjamin Franklin. One of Franklin’s many pursuits in life was to obtain a perfect moral character. He set a personal goal for himself to essentially emulate a character like Christ and live without any faults whatsoever at any time.

Franklin created a spreadsheet that tracked thirteen virtues, ranging from “Temperance” to “Humility,” which he would review each day and note wherever he fell short or failed. If he drank one mojito too many, for example, he’d write an “x” in that day's Temperance column. The next day, he'd know to keep an eye on his booze consumption.

After doing this exercise for years, he realized that while he became an overall much better person and even obtained near-perfection in certain virtues, he fell terribly short in others. In particular, he never made much progress in the virtue of “Order” which he defined as “let all your things have their places; let each part of your business have its time.”

In his words:

Order…I found extremely difficult to acquire….This article, therefore, cost me so much painful attention, and my faults in it vexed me so much, and I made so little progress in amendment, and have such frequent relapses, that I was almost ready to give up the attempt and content myself with a faulty character in that respect.

Not one to readily admit defeat, he asked himself if it was worth giving his more stubborn flaws extra attention. After all, isn't the whole point of self-improvement to acknowledge and battle our slothful, fixed nature head-on? Shouldn't we exert ourselves twice as hard in fixing those flaws that seem the least likely to change?

Or should we instead get comfortable with the idea that we are flawed in our own particular way and that each of us may have only so much room to improve in certain areas?

Ultimately, Franklin answers with the story of the man who bought an ax from a blacksmith and requested that its surface be made as bright as the edge:

The smith consented to grind it bright for him if he would turn the wheel; he turned, while the smith pressed the broad face of the ax hard and heavily on the stone, which made the turning of it very fatiguing.

The man came every now and then from the wheel to see how the work went on, and at length would take his ax as it was, without farther grinding. "No," said the smith; "turn on, turn on; we shall have it bright by and by; as yet, it is only speckled."

No Man Is An Island

We like to believe that our thoughts and emotions are ours and ours alone. We are independent entities capable of thinking for ourselves and rising above the groupthink and mania all around us.

Had we been in Germany in the 1930’s, we tell ourselves that we would have seen the evil of the Nazi party for what it was and refused to get swept away in the madness. Had we been in the South in the 60’s, we would have rejected the racist worldview of our peers and marched alongside the civil rights leaders of the day. Had we been at a Pitbull concert last week, we wouldn’t have let an energetic crowd trick us into believing the guy actually has talent.

We are not sheep, we like to believe. We are immune to the manic and irrational behavior of groups. We are beacons of rationality and independent thought. It’s ridiculous that nobody has made a statue of us yet. We are Athena herself reincarnate.

But, what if that’s not even close to being true? What if we’re blind to a deep impulse that makes us more dependent on each other than we’d like to admit?

Humans have a deep impulse to mirror the behavior of the group, and it kind of makes sense

Robert Greene dropped a book this week, The Laws of Human Nature, that I’m convinced will be talked about for the next 30 years. For those unfamiliar with Robert, he spends years upon years writing his books, most of which are about human psychology. The Laws of Human Nature is the culmination of more than 20 years of what he’s learned about how humans behave and think.

One chapter that was particularly striking described the impulse that humans have to conform and mirror the behaviors of those around them. Being a conformist tends to get a bad rap these days, but Greene gives the behavior a rational basis in our evolution as a species. While it's far from the only reason we tend to behave like others, it's not one that's written about often.

To survive, humans needed to mirror the emotions of others

If you and your homies went hunting in the Savannah 50,000 years ago and somebody in the group saw a scary-ass tiger, teeth out, charging directly at the group, time was not on your side. Whoever saw the tiger didn’t have the luxury of calling a team meeting, “hey gang, everybody have a minute? I was hoping to convince each of you that a tiger is rapidly approaching and is about to remove our faces from our bodies.”

It was crucial that the group immediately feel the same fear of whoever witnessed the threat. The quicker the fear could spread through the group, the sooner everybody could react and the more likely they all were to survive. Species that could share emotions, rather than letting them remain the experience of a single individual, maintained an evolutionary advantage in certain contexts.

Our emotional lives are deeply intertwined with those of others

This impulse to mirror the emotions of others clearly goes beyond life-or-death situations. If we’re in conversation with somebody who’s good-spirited and energetic, for example, we’ll notice our own mood gradually lift. And when somebody is being a Negative Nancy, we can watch as their toxic attitude gradually infects those around them. Emotions - some strong, some subtle - often ripple through groups rather than staying bottled up in any individual.

What is true of emotions also seems true of opinions and worldviews

Imagine we’ve been momentarily infected with a negative attitude after an encounter with a walking, talking bummer of a human being. We’re exhausted and de-energized and our emotions often spill over into our worldview. Far from just “feeling tired,” our understanding of reality is momentarily altered. Our beliefs about the future, for example, are likely to be different if we’re feeling exhausted and beaten up than if we’re feeling juiced up and thrilled to be alive.

So, emotions influence our worldview and our emotions are often not really “ours," per se. We are temporary hosts for various states of conciousness, and very often their corresponding worldviews, as they ripple through a group.

This propensity to absorb and transmit emotions is deeply embedded in our nature, making us far less of an island than we might imagine.

Today, emotions can ripple through society ludicrously fast and at a ludicrous scale

Over the past few decades, our role as an Emotion Transmission Beacon has been able to play out at an increasingly enormous scale.

Today, somebody can experience some horrific injustice, post a message or video on Twitter, and within hours, righteous outrage will radiate through millions of other people — much in the same way that the fear of the point man in the Savannah radiated through his tribe members.

Our emotional lives are deeply intertwined and we are not quite the independent actors we’d like to imagine.

We are nodes in a deeply interconnected web of emotions that ebb and flow between all human beings.

Benjamin Franklin's Long Road To Becoming A People Person

Benjamin Franklin was one of the greatest statesmen in all of human history, navigating some tumultuous times with tact that few of us can imagine. The man had a rare ability to get insanely difficult people to cooperate and get things done.

But it turns out that Franklin wasn’t born with this natural tendency to work well with others. He was terrible at reading people in his youth and it got him in a ton of trouble.

Robert Greene, in his incredible book Mastery, shares a few examples of Franklin’s early follies in dealing with others. Taken together, they contain tons of practical wisdom for the rest of us:

1. A teenage Benjamin Franklin pisses off his older brother

From a young age, Benjamin Franklin dreamed of becoming a successful writer. Luckily for him, his older brother James was opening a print shop in Boston. He went to work for his brother, aspiring to one day have his own work published. In addition to doing crappy apprentice tasks, Franklin would pitch story ideas to his brother who constantly shot them down, claiming that readers of The Courant would have little taste for Franklin’s writing.

So, Franklin began to submit letters to his brother’s paper under a pseudonym. He invented a young female widow named Silence Dogood who wrote highly opinionated, sometimes absurd, essays about life in Boston. Her letters quickly became one of the most popular section of the newspaper.

One day, smug with the success of Dogood’s letters, Franklin revealed to his brother that Dogood was his creation. Rather than praising Benjamin for his exceptional writing and the attention it had brought to the paper, James was furious. He hated being lied to and needed loyal foot soldiers in the shop, not rebellious, aspiring creatives. Benjamin’s relationship with his brother deteriorated to the point of his brother becoming abusive, and Franklin eventually fled from Boston and moved to Philadelphia.

2. Benjamin Franklin gets swindled by a conman governor

Once in Philly, word of Franklin's publishing expertise got around. The governor, William Keith, was not happy with the only two printing houses in Philadelphia and sought out Franklin to help him start a third; he’d even fund the whole thing himself. Keith told Franklin to travel to London, where machines and material would be waiting for him. Amazed by his good fortune, Franklin abruptly quit the job with the printer he had just landed in Philly and shipped off across The Atlantic.

Once in London, a wealthy merchant told Franklin that the governor of Pennsylvania was a notorious talker, obsessed with projecting an image of power, wealth, and success, but in reality his pet projects rarely lasted more than a week and he didn’t even have the cash to back them up. It dawned on Franklin that he was stuck in a foreign country where no money, no machinery, and no materials were waiting for him.

3. Franklin pisses off his co-workers

With no means to get home, Franklin picked up a job at a printing house in London. His co-workers loved to drink on the job, routinely taking breaks to throw back a pint. Franklin was expected to contribute to the employee beer fund, but he informed his co-workers that he did not like to drink while he worked and, as a man of principles, would not be contributing to the fund.

Over the next few weeks, his co-workers began to sabotage his work. Typos began to pop up in work that Franklin had already edited and he was continually blamed for a never-ending stream of reckless errors. It eventually dawned on Franklin what was going on and he begrudgingly contributed to the beer fund.

So, there you have it. One of history’s greatest statesmen began his life as a clumsy, naive, clueless punk who pissed off or misread tons of the people around him.

"With his brother," Robert Greene writes in Mastery, “[Franklin] wanted to impress him by revealing his authorship of the letters, totally unaware of the envy and malevolence he would unleash; with Keith, he was so wrapped up in his dreams that he paid no attention to obvious signs that the governor was all talk; with the printers, his anger blinded him to the fact that they would obviously resent his attempts at reform.”

After these and a few more incidents, it dawned on Franklin that much of his suffering in life stemmed from an utter and complete failure to consider the motivations of others. When he wrote the Silence Dogood letters, he was able to put himself into the mind of another, obsessing over how she perceived the world. Yet, he failed to make even the most basic effort to do this with the people around him.

Franklin pledged that he would no longer be at the whims of his own insecurities and emotions, and would instead try to understand people for how they actually were, not how he lazily assumed or hoped they would be.

A new, less-dumb man is born

Franklin finally found his way back to Philadelphia and was immediately offered his job back by Samuel Keimer, the printer whom he had previously bailed on just before his trip to London. It didn’t take long for Franklin to detect that something was up; why was Keimer being so hospitable to a guy who had ditched him a couple of years prior?

It dawned on Franklin that Keimer wanted to extract all of Franklin's publishing expertise, teach it to his employees, and then fire him. Realizing that the clock was ticking, Franklin quietly turned the tables and used his relatively high-ranking role at Keimer's shop to begin networking around town. By the time it became obvious that Franklin was about to be canned, he had already built up a network of backers ready to support him in opening up his own shop, which is exactly what he did, ditching Keimer once again and going on to be a successful newspaper publisher and best-selling writer.

In Greene’s words, “In executing this strategy, Franklin noticed how free he was from any feelings of bitterness or anger toward Keimer. It was all maneuvers on a chessboard, and by thinking inside Keimer he was able to play the game to perfection, with a clear and level head.”

If Benjamin Franklin had to work hard to understand other people, you and I probably have some work to do

Franklin's naivety as a young man does not represent some childish state that we naturally outgrow as time goes on; it’s the default human worldview that persists at all ages. For whatever reason, we are convinced that our own little story is the most interesting one on Earth. We have little interest in understanding the motivations and perspectives of others because the most addictive movie on the planet is playing out in our head at all times. Why change the channel?

This tendency blinds us to the fact that people are revealing their intentions, motivations, and worldview to us all the time. Very often, we totally miss this and instead project our own insecurities, biases, naivety, and emotions onto others, assuming them to be something other than what they are.

If we don't strive to consider the perspectives of those we interact with, we end up on some spectrum where the best case is constantly boring those around us with our self-interested ramblings and the worst case is reliably being taken advantage of because of our blindness to the true motivations of others.

Franklin was onto something when he realized the value in shutting the hell up and listening every once in a while.

Writing is a brutish, torturous exercise. Even the world’s greatest authors lamented how much it sucks to sit down and commit ideas to paper.

“When I write, I feel like an armless, legless man with a crayon in his mouth.”Kurt Vonnegut

That’s right; a mind who defined a literary generation felt anything but competent as he did it.

“Writing a book is a horrible, exhausting struggle, like a long bout with some painful illness. One would never undertake such a thing if one were not driven on by some demon whom one can neither resist nor understand.”George Orwell

George Freaking Orwell didn’t whistle while he worked.

“A writer is somebody for whom writing is more difficult than it is for other people.”Thomas Mann

I have 47 browser tabs open right now and will keep hurling these at you until you’re convinced.

"Writing books is the closest men ever come to childbearing."Norman Mailer

“I write the way women have babies. You don't know it's going to be like that. If you did, there's no way you would go through with it.”Toni Morrison

There are tons of things that make writing hard, but here's one that's not talked about often: writing forces the author to face their own inadequacies in a way that’s nearly impossible elsewhere in life.

When you sit down to write, one thing is immediately apparent: anything that sucks is completely your fault.

All of the lazy assumptions, the half-truths, the naivety, the reliance on cliche, the uninspiring and unoriginal ideas, the failure to persist and land on real insight, to miss the bigger point, using language because it’s convenient rather than precise, all of it, every failure to produce something worth reading, is the writer’s to own. You can blame your mom if you want, but it’s not going to put the next word on the page.

This stands in contrast with much of the rest of life, where execution happens against a myriad of factors outside of ourselves; the politics at this place make it impossible to get stuff done, some idiot got into a fender bender and made me late, the wifi at the airport Arby’s was crappy so I couldn’t finish that research, the sandwich I ate at said Arby’s has made me violently ill and I may only have moments to live, and so on. Those are all reasonably clever excuses.

But there’s a brutal clarity in the world of the writer; if what she writes sucks and it's only her, the pen, and the paper, it’s pretty obvious who's at fault.

The fact that most situations aren't as simple as the writer's doesn’t necessarily make what’s true in one world any less true in the other. Maybe we do have more agency than we think, but we’re blind to it because whenever our identity as competent and capable people is threatened, we turn on Blame Mode™ and scan the rich and complex situations around us for any plausible target other than ourselves to attribute failure. This is like shooting fish in a barrel most of the time, sparing us the discomfort of looking inwards that a simpler set of circumstances would have forced upon us.

So, yeah, writing is hard because you have to accept responsibility for your actions, which says a lot more about human nature than it does about writing.

The Internet's Opportunity Machine

The past couple of Stew’s Letters (part one, part two) have made the case that if you can learn how to do something that society is unable to teach, and it just so happens that your “something” is valuable, you may be rewarded handsomely since you’ll have little or no competition.

This is more of a mental model more than it some clear game plan, but it stands in contrast to the more traditional approach to career planning where we look at what the world is hiring for today, invest in formal training, and begin to climb the metaphorical ladder in our chosen field, mostly keeping our skillset within the boundaries defined for us by the system we’ve chosen to be a part of.

The traditional approach makes practical sense and I don’t doubt it still works in plenty of contexts today; it’s also the only realistic road for a huge number of people. But, the rise of the internet over the past two decades has opened up enormous opportunities for those of us who want carve out our own niche in the universe rather than occupying a toe nail of a somebody else’s.

What’s so special about the moment in history we’ve found ourselves?

The internet is an opportunity machine that does one thing particularly well: it creates a playing field where seemingly obscure, niche things have a far higher likelihood of becoming a successful business than ever before.

First, a quick refresher on what the world looked like in the not-too-distant past.

WARNING: MANY OBVIOUS IDEAS FOLLOW

Much of what’s in this essay might seem painfully obvious, especially to anybody who thinks much about the internet’s impact on society. This essay was almost buried forever in the draft folder because of how “duh” some of it sounds. After working on it a bit more though, I found that articulating these ideas was helpful in revealing how often I fall back into a pre-internet understanding of the world.

So, with that, you’ve been warned.

What the world used to look like

For the past hundred or so years, the world has looked something like this:

A handful of companies controlled the means of distribution and defined a relatively narrow set of goods and services that represented our choices as consumers. In the U.S., all of us watched some subset of the same TV channels, every grocery store in town stocked identical brands of soap and cereal, and it didn’t make a difference whether you went to a movie theater in LA or Des Moines — the same ten movies played at both.

This narrow list of choices we all had as consumers wasn’t necessarily part of a conspiracy concocted by a few mustache-twirling capitalists; it was largely the practical result of how expensive it’s been for most of human history to produce, market, and distribute products.

Safeway was not going to drop millions of dollars on a new grocery store only to stock its limited shelf space with Larry’s Magic Healing Crystals™. Each store needed to be filled with affordable, mass-manufactured items that appealed to a broad audience. There was no space for the obscure, niche stuff that didn’t sell well.

The same was true of a retailer like Barnes & Noble who was not going to drop a few million bucks on a new bookstore only to line the shelves with Great Heroes of Frisbee Golf, Volumes Seven through Twelve (1936-1975). There are more Stephen King fans than frisbee golf connoisseurs and B&N ain’t running a non-profit.

All of this was bad news for people who had a message or a product that might not hold mass appeal. There may have been plenty of frisbee golf fans around the world who would love the entire Great Heroes of Frisbee Golf series, but very few in each submarket. And without a major distribution deal most frisbee fans were unlikely to even hear of your book, making it even harder to prove demand and convince a big retailer to carry you in the first place.

Chicken, meet egg.

The internet is taking a sledgehammer to the chicken-or-the-egg problem, though, and is leaving nothing but scattered bits of shell — and opportunity — in its wake.

You can’t spell “opportunity” without “awareness”

Fun fact: you can’t capitalize on an opportunity that you’re not aware of. You also can’t buy a book you’ve never heard of. And you definitely can’t order a set of Larry’s Magic Healing Crystals™ without first knowing they exist.

It follows, then, that the ability for information to move between humans is the lifeblood of opportunity. And for most of human history, it’s been a huge pain in the ass to move around information. It’s easy to forget that this is was what cutting-edge global communication technology used to look like:

Pictured: the internet, 350 years ago

Today, half of the Earth is hooked up to each other via cheap, accessible computers that serve as opportunity machines, removing an enormous amount of friction in our ability to transmit information and hear about things that might deeply interest us, improve our lives, etc.

Let’s reflect on just how far we’ve come:

So what are the tangible impacts of our newfound ability to move around information quickly and cheaply? More specifically, how does it affect the nature of economic opportunity?

There are at least two big things that the internet has done, and both have direct implications for how we can make money and build a career. They’re probably conventional wisdom at this point, but let’s do a quick refresher on what they are.

1. The internet has brought the cost of distribution for digital goods down to essentially nothing.

It’s pretty wild to remember that Barnes & Noble, a seller of ideas, has historically been stuck playing the same game as Safeway, a seller of tomatoes and beef. Before the widespread adoption of cheap personal computers, ideas had to be captured in a physical form (a book, novel, encyclopedia, etc.) and were thereby subject to the same laws of physics and markets as the stuff you find in the grocery store.

For those reasons, Great Heroes of Frisbee Golf, Volume Seven (1936-1945) would have had a hard time finding an audience at all.

But, the internet has brought the cost of distribution down to essentially zero for products that can be represented in a digital form. Now, an entire frisbee golf book series can obviously just live on Amazon’s digital shelves as an ebook incurring negligible cost for the publisher or Amazon. Having a book in the “Long Tail” of book rankings doesn’t mean the certain death it may have in the recent past.

2. The internet has made it remarkably easy to find and reach the people who will love your product, song, book, class, whatever.

The geographical boundaries that have long defined tribes are melting away, leaving only ideological ones.

Instead of taking out an ad in a local paper in the hope of finding a few people who might buy whatever you’re selling, you can get on Twitter, search for people everywhere on Earth talking about ultra-specific topics, and send them a direct message that will almost certainly land it in front of their eyes — for free or next to nothing. The friction is becoming so incredibly low to locate, qualify, and get a message to the right people.

1 + 1 = ?

Taken together, these two forces are driving some enormous changes in the economy.

“The Market” is breaking into niche markets where there were none before

In a nutshell, the internet enables sizable niche markets to exist where they simply couldn’t before. For example, imagine if you were a budding (bubbling?) soap entrepreneur twenty years ago. That would would have been pretty brutal.

Generally speaking, if you wanted your soap line to make any real money, you had to go head-to-head against the big boys and try to convince a major distributor to carry you alongside them.

Today, you could circumvent the system altogether by hosting a Shopify store and distributing, marketing, and selling the soap yourself. The challenge shifts from the nearly-impossible task of getting into a major chain store to the difficult, but less existentially-risky task of finding and broadcasting a message directly to the people who will love your product.

In theory, the internet enables a thriving long tail of soap products to exist.*

So, maybe we should be skeptical when we ask “how do I convince a major retailer, publisher, studio to buy into what I’m doing?” Instead, we can opt for “how do I find the end customers who will love what I’m selling so that I can remove the middleman altogether?”

* In practice, I have done absolutely no research on the soap industry.

Many of these “niches” are huge

It’s easy to hear the word “niche”and imagine a market that is almost trivially small. Aw, is that your niche over there? So cute.

But the internet keeps revealing just how many enormous, untapped niche markets exist — granted, at some point these things probably become way too big to be considered a “niche” at all.

One place where is blindingly obvious is in the media industry, as demonstrated by people like Logan Paul. For better or worse, he’s proven that millions of people are apparently interested in watching a person with a double-digit IQ insult Santa Clause in a self-produced rap music video entitled “SANTA DISS TRACK.” That video alone has garnered over 64,500,000 million views, vastly more than most major media companies could ever hope to attain with their best content.

For context, here’s how The Oscars did last year:

This phenomenon is showing up all over the place. Take Delighted, a company that pulls in millions of dollars every year by making it easy to embed a “how likely are you to recommend this to a friend” survey into your website. That’s a hilariously specific business. Or MVMT, who brought in $70 Million last year selling niche watches on Instagram.

Hell, take Scrivener, the software I’m using to write this. A school teacher in London built the first version in his spare time ten years ago and started selling it for $50 a pop to writers. It’s now a real company with a real team and real revenue. To get even more niche, there’s also apparently some dude who made half a million bucks teaching people how to use Scrivener. Niche-ception! It’s madness, and neither of these businesses could exist without the internet.

The takeaway? An ever-increasing amount of the Long Tail is economically sustainable. It used to make sense to kill a business idea quickly because it was not immediately obvious that there was a big enough market for it. But, today, maybe we should think twice and consider how much easier it is to find the people who will love what we’re doing.

Bonus points: we may have more freedom to not water down our work

When the distribution channels in an industry are expensive and tightly-controlled, there’s often pressure to water down what goes through it in an attempt to make it more “appealing” to a mass audience. I know my boy Joel Osteen would say even crazier stuff if he didn’t have a publisher.

Jenny Han felt this pressure to sell out before finally getting her movie “To All the Boys I’ve Loved Before” made. Every major studio except Netflix said they’d only cast a white, not an Asian-American, actor as the lead. Yikes.

It’s our job as professional niche-hunters go directly to the 100,000 people who will love what we’re doing and forget about the million who might kind of like it if we toned it down a bit.

The Age Of The Niche has only just begun

“People don’t have any idea yet how impactful the internet is going to be and that this is still day one in such a big way.” - Jeff Bezos

We’re still in the early days of the internet, which could mean we’re only just beginning to see what the niche economy looks like. And if the future looks anything like the present, then opportunities await those willing to combine their skills in a unique way to conquer some exciting niche.

Happy hunting!

An honorable mention is due to the great, short book “The End Of Jobs” which elaborates on and inspired many of the ideas here.

The Art Of Unstructured Learning

Last week's Stew's Letter was all about a simple idea: if society can train you to do something, it can train somebody else and replace you. One strategy to escape the proverbial rat race, then, would be mastering a valuable combination of skills that society doesn't yet know how to teach.

If we can combine a handful of skills in a way that the world hasn't quite seen before, and it just so happens that the combination is valuable, we get to reap all the rewards until society catches on and boils what was once our genius into a curriculum and a "career path."

This is in contrast to our more natural tendency to look at what skills the world is hiring for today and reshaping ourselves accordingly. Even a 22-year-old Hunter S. Thompson insisted we resist this urge:

Let’s assume that you think you have a choice of eight paths to follow (all pre-defined paths, of course). And let’s assume that you can’t see any real purpose in any of the eight. THEN— and here is the essence of all I’ve said— you MUST FIND A NINTH PATH.

Full disclosure: I don't feel remotely qualified to write about this topic and it seems worth mentioning that Hunter S. Thompson took his own advice to an extreme and lived a life I'm not sure I envy (insane drug use, getting into gun fights with his neighbors). But, alas, I feel compelled to write about this so buckle up.

Our quirks can be strengths

At some point, many of us have probably faced the proverbial - or literal - bully who has mocked or trivialized something that makes us stand out.

In my case, a bully in middle school preyed on the fact that I was overly-friendly and physically incapable of defending myself; I was "soft," as the youths say. He would threaten to beat my ass if I didn't give him my lunch money each day.

Instead of starting to lift weights so that I could be the one smashing faces in, I doubled down on the exact things he hated (my ability to connect with people) and ended the year with an alliance of thugs-turned-friends who defended me and forced this douche canoe to set his sights elsewhere.

"Quirks" are often rare skills in disguise.

We all have potentially valuable quirks

Imagine for a moment that you're a salesperson who can write well. Or a software developer who loves design. Or an operations guy who's a talented DJ. Or a climate scientist who can give a presentation without sending her audience into REM sleep. Those are all rare combinations of skills that could lead to some magical places.

A sales guy who can write well might escape the most crowded sales channel - taking clients out to drinks - and instead close a huge deal in a persuasive email that pierces through the sea of bullshit his peers are trapped in. Maybe the DJ COO could write a song every quarter that'd be entertaining enough to make people care about boring but important stuff. And so on.

Far from being static, the games we find ourselves in can be reshaped depending on the skills, talents, and personalities of those playing them.

All of us have a unique skill salad - a "skill stack" to rip off Scott Adams' terminology - that we can cultivate if we're willing to look inwards, find a few magic ingredients, and stay committed to nurturing and growing what we find even if we're not seeing any job descriptions that fit the bill yet.

Quote From Smart Person That I Probably Could Have Just Shared And Skipped Writing The Previous Section Altogether

“Those qualities that separate us are often ridiculed by others or criticized by teachers. Because of these judgments, we might see our strengths as disabilities and try to work around them in order to fit in. But anything that is peculiar to our makeup is precisely what we must pay the deepest attention to and lean on in our rise to mastery.” - Robert Greene

Turning quirks into superpowers

Okay, so assume you have a hunch on what your skill salad looks like. You're pretty good at a few things and have a gut feeling on how they might be combined into something valuable. What do you do next?

Improving each individual skill is straightforward enough. If you want to get better at boxing, just go find a gym, hire a trainer, and spend your spare time watching boxing videos on YouTube. It might take a while, but there's a known path to nailing down the basics.

But, what happens after you've become a decent fighter? You're ready to synthesize some of your other talents and create a unique fighting style. Surely there's some curriculum that can take you from competence to mastery?

Nope.

Unfortunately, mastery doesn't appear to be an emergent property of building up various hard skills on their own. We have to go a step further and continually experiment with how to best synthesize our seemingly unrelated talents into a cohesive whole.

Tim Urban from Wait But Why didn't just get really good at writing and then get really good at drawing comics and all of a sudden give birth to his incredible blog. Instead, there's a theme of trial-and-error in his work as he's combined the two skills, eventually culminating into the genre he's known for today.

So to become great at something new, we'll need to figure stuff out on our own and leave the comfortable world of structured learning. We must enter the hairy, ambiguous, no-handbook dimension of knowledge formation known as “unstructured learning.”

Welcome to hell: unstructured learning

Unstructured learning lacks a clear curriculum. There are no exercises with pass/fail criteria, nor a handbook on how to move from the basics to mastery. It’s arguably the hardest kind of learning, but it's likely to pay the greatest dividends. After all, knowledge that can be distilled into a curriculum can be taught to somebody else who's smarter and cheaper.

So how are we supposed to learn something that can’t be taught?

Unstructured learning by definition does not have a how-to manual. So rather than pretend I know how to best navigate the murky road towards carving out a valuable niche in the universe, I feel compelled to do two things:

1. Acknowledge that unstructured learning exists.

Unstructured learning is a thing and it's required for doing anything remotely interesting. Maybe everybody already knows that, but there can be value in reminding ourselves of the obvious; in this case, that originality is always preceded by ambiguity.

2. Share a few nuggets of wisdom that seem relevant for those inclined to venture into the unknown.

As I was writing an early draft of this post, one of the smartest human beings I’ve ever crossed paths with published a short piece on how to learn stuff that no one can teach you. It contains some timeless wisdom for the restless and curious, but for those short on time here are two big ideas about unstructured learning that stuck with me:

Big Idea #1: You Have To Fight For Your Knowledge

You're not going to learn much if you view knowledge as something that schools, bosses, mentors, family members, and the universe owe you. That's lame and false.

Knowledge is more like the last helicopter out of 'Nam. You'd better go find it and fight like hell for your seat.

Unfortunately, most of us don't fight for our seat on the proverbial knowledge-copter. If we don’t understand something after our first question, we give up. We figure that maybe we don’t deserve to know. It's tragic, of course, because we do.

“Learning is sacred and everyone deserves it. That includes you.”

Big Idea #2: Short-Term "Stupidity" Is The Key To Long-Term Mastery

We spend much of our lives in systems that reward the appearance of competence, which makes sense most of the time. Schools probably shouldn't give A's to kids who answer every question with "I have no clue" and companies probably shouldn't promote people who don't know how to do their job.

But, one unintended consequence of constantly keeping up appearances is that we become terrified to look stupid. People who show vulnerability or admit ignorance get stepped on, or so we tell ourselves.

Looking stupid in the short term, though, is the exact thing we most need to do to accelerate our learning. Our job is to eliminate our ignorance as quickly as possible and there are fewer faster routes than asking obvious, “dumb” questions early and often.

Doing this might come with short-term social consequences, but what's worse over the long term: looking dumb or actually being dumb?

"But my skill salad can't make money"

Okay, assume you've gotten this far. You're ready to blaze a new path and show the world your genius. There's just one problem: it's not immediately clear that you can make money from what you're good at.

That's a valid concern, but I implore you to at least consider the following case study:

In conclusion...

"Jesus Christ, this is a long Stew's Letter. We gonna wrap this up anytime soon?"

Alright, so there you have it. A whole bunch of repurposed thoughts on why blossoming into a unique butterfly might not be a terrible life strategy and how you might be able to navigate the inevitable ups and downs required to get there.

This is obviously just one of many ideas on how to build a career and life, though, and I won't pretend that it's complete, or right for everybody, or even terribly practical. But if you've made it this far, I hope you'll at least consider looking inwards and figuring out the things that only you can do.

It'd be pretty messed up if you didn't share your genius with the rest of us.

Footnote: Another excellent life strategy is having a rich uncle die and leave you a fortune. That strategy has a 100% success rate and if you can pull it off, you should. I repeat: if somebody wealthy is planning to give you a large sum of money, don't waste your time building up a skill salad; just kick back and don't screw it up.

Part One: I've Got 99 Problems, And Creating A Lucrative Career Niche Is Absolutely One

My name is Stewart and I want to have an amazing career. It's pretty straightforward: I want one of those careers where you work day in and day out on the singular thing the universe has called you to do. One where you make enormous sums of money, never miss your kids' soccer games, and experience a state of flow that doesn't just muddy the definition of the word "work," but makes one pity the poor rubes forced to experience displeasure in any form in exchange for compensation.

There's one problem though: society has failed to produce a handbook on how to obtain a career that offers those things. Hell, I've never seen a job description that includes even one of them. It's ridiculous, I'm pissed, and I guess we're just left to figure this stuff out on our own.

So, let's start.

If You Can Be Trained, You Can Be Replaced

Those of us in careers with a relatively low barrier to entry are subject to an unpleasant reality: if society can train us to do something, it can train somebody else and replace us. Many of us are more replaceable than we want to acknowledge or admit.*

And if society can easily replace us, it’s generally going to be harder for us to make fat stacks of cash. There will always be somebody else out there willing and able to do the same job for less.

So, that’s not great news for those of us who don’t plan on dropping everything, going back to medical school, and entering a field with an insanely high barrier to entry. How the hell are we supposed to end up with an amazing career?

Escaping Competition: Your Unique Skill Salad

One strategy I’ve been thinking a lot about is creating and mastering a unique combination of skills that society needs but hasn't realized it yet. The skills themselves may be familiar, but the combination is new and valuable.

If society hasn't seen a particular combination of skills before then it definitely hasn't figured out a way to teach it to other people yet. If you figure out a good recipe, it's yours to own until the rest of the world catches up.

The concept of being a full-time inventor, for example, was relatively new in Thomas Edison's day, leaving him little competition. A century later, we've built up a huge infrastructure to support and train people to do research and development for new technologies that might have potential commercial applications.

What seems obvious today - a combination of scientific aptitude and business savvy is valuable - was at some point an entirely new insight.**

"If the path before you is clear, you're probably on someone else's."

Anybody who wants to carve out their own lucrative career niche, by definition, cannot look at somebody else's path and try to mimic it. Instead, maybe they could look at the raw ingredients right in front of them - their skills and interests - and see if there's a valuable combination that the world hasn't witnessed.

The world often nudges us to make the best ham sandwich we can, but maybe we should just get out whatever the hell is in the fridge and see if we can't put together something new and awesome instead.

Quote From Smart Person That Totally Backs This Up

"All successful CEO's are like this. They are almost never the best product visionaries, or the best salespeople, or the best marketing people, or the best finance people, or even the best managers, but they are top 25% in some set of those skills, and then all of a sudden they're qualified to actually run something important."- Marc Andreessen

Anecdotal Example That Totally Proves My Point

Tristan Harris was essentially a dime-a-dozen software engineer then product manager (not rare, moderately valuable) at some of the large tech companies before he carved out a niche as a product “philosopher” (non-existent role until him) and ethical thinker at a time when society was just starting to grapple with the newfound consequences of what had up until then seemed inherently harmless or even trivial.

Most of his peers are probably competing for the same product manager roles while Harris is now in a league of his own, founding a school of thought in a valuable niche for which he’ll be the go-to guy for the foreseeable future.

Okay, so I've finally convinced you. You've decided that you’re going to become the world’s first self-driving food truck machine learning engineer. Udacity doesn’t have a course on that, so what the hell are you going to do?

Stay tuned for Sunday's Stew's Letter, dear reader.

* The barrier to becoming a reasonably competent software engineer in certain domains is just not has high as many of the pre-madonnas in the field would lead you to believe. And I don't have time to elaborate so stay the hell out of my DMs.

** Granted, the world changes and makes the same combination of skills more or less valuable depending on where in history you exist. Being a great singer during the Ice Ages probably didn't pay out in the same way it does today.